Sulfur-containing volatile organic compounds in cannabis

ABSTRACT

An edible composition, an aerosol composition, a flavor composition, a fragrance composition, or an inhalable composition includes an organosulfur compound such as prenyl mercaptan, 2-methylthiophene, 3-methylthiophene, dimethyl disulfide, diprenyl disulfide, 3-methyl-2-buten-1-yl thiolacetate, 3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol (1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate, thiogeraniol, dimethyl sulfide, or a combination of any two or more thereof, and a primary terpene compound selected from the group consisting of myrcene, β-caryophyllene, limonene, α-pinene, β-pinene, valencene, ocimene, terpinolene, or a combination of any two or more thereof.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional Application No.62/963,615, filed Jan. 21, 2020, and U.S. Provisional Application No.63/005,678, filed Apr. 6, 2020, the disclosures of each of which areincorporated herein by reference in their entirety.

FIELD

The present invention relates to various compositions, products, andmethods that are capable of, or adapted to, providing, augmenting, orenhancing the gassy odor or aroma. In particular, the present inventionrelates to organosulfur compound containing compositions products, andmethods that are capable of, or adapted to, providing, augmenting, orenhancing the gassy odor or aroma.

BACKGROUND

The following discussion is provided to aid the reader in understandingthe disclosure and is not admitted to describe or constitute prior artthereto.

Cannabis is one of the most popular recreational drugs and it hasrecently seen significant changes to its legality within the UnitedStates and other countries. The Cannabis plant has many unique traits,such as its ability to biosynthesize a wide variety of secondarymetabolites including tetrahydrocannabinol (THC), cannabidiol (CBD), aswell as a plethora of monoterpenes, monoterpenoids, sesquiterpenes, andsesquiterpenoids. Although typically consumed for the psychoactiveeffects brought upon by THC, and more recently proposed therapeuticeffects of CBD, recent interest within the greater cannabis communityhas turned to terpenes and other compounds that give cannabis its uniquescent and flavor. Like THC and CBD, the concentrations and types ofterpenoids present are heavily influenced by both genetics and externalstress on the plant throughout the growth cycle. Through selectivebreeding, growers have been able to produce plants with a wide varietyof aromas, all primarily due to the presence of compounds of the terpeneclass.

The major or primary aroma compounds contributing to the odor ofcannabis as described in scientific and popular literature areβ-Myrcene, α- and β-Pinene, D-Limonene, β-Caryophyllene, Terpinolene,and Humulene, although over 200 compounds have been described throughoutthe scientific literature. The presence of various secondarymetabolites, terpenes, terpenoids, sesquiterpenes, and sesquiterpenoidsresults in Cannabis products having a wide variety of aromas and flavorswith remarkable depth and complexity. One of the most popularorganoleptic descriptors in Cannabis is the presence of a “Gassy”aroma—that is, an aroma that emulates that of gasoline. This aroma isdescribed as a piercing, sulfuric, sharp odor on the nose that is oftenassociated strongly with strains of the OG family, although otherfamilies can likewise have similar odors. It is also commonly consideredan indicator of freshness and/or quality of a cannabis product. Althoughcannabis breeders can breed plants to express specific odors, such asthis odor, the exact chemical composition that leads to it is unknown.Within the cannabis community, much focus has been on terpenes,sesquiterpenes, and their oxygenated derivatives. However, attempts atemulating certain aromas using artificial blends with many of thesecompounds in ratios determined from gas chromatographic data have fallenshort when capturing the complete aroma profile of a given cannabisstrain. One strain family that has been notoriously difficult to emulateis the OG family, pioneered by the strain OG Kush. This strain ischaracterized by what is often described as the quintessential aroma ofcannabis—a strong, sulfuric, gassy odor that has a highsubstantivity—the ability for an odor to be detectable over a period oftime. This strain has subsequently been cross-bred with other strains,leading to a plethora of strains that now possess this pungent odor.Attempts at using chemical characterization methods such as gas orliquid chromatography have not led to an obvious origin of this odor incannabis, and thus remains somewhat of a mystery regarding whatcompound, or compounds, contribute.

SUMMARY

According to a first aspect, a composition comprises an organosulfurcompound selected from the group consisting of prenyl mercaptan,2-methylthiophene, 3-methylthiophene, dimethyl disulfide, diprenyldisulfide, 3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, dimethyl sulfide, or a combination of any two or morethereof, and a primary terpene compound selected from the groupconsisting of myrcene, β-caryophyllene, limonene, α-pinene, β-pinene,valencene, ocimene, terpinolene, or a combination of any two or morethereof, wherein the composition is an edible composition, an aerosolcomposition, a flavor composition, a fragrance composition, or aninhalable composition.

In certain embodiments, the composition comprises about 0.000001 wt % toabout 0.3 wt % of the organosulfur compound, based on the total weightof the composition. In certain embodiments, the organosulfur compoundcomprises prenyl mercaptan, prenyl thioacetate, or 2-methylthiophene.

In certain embodiments, the primary terpene compound is present in anamount of from about 0.1 wt % to about 99 wt %, based on the totalweight of the composition. In certain embodiments, the primary terpenecompound is present in an amount of from about 0.1 wt % to about 90 wt%, based on the total weight of the composition. In certain embodiments,the composition further comprises a secondary terpene compound selectedfrom the group consisting of humulene, linalool, bisabolol, nerol,phellandrene, terpineol, farnesene, fenchyl alcohol, geraniol, menthol,citronellol, citronellal, geranyl acetate, nerolidol, citral, or acombination of any two or more thereof. In certain embodiments, thesecondary terpene compound is present in an amount of from about 0.01 wt% to about 50 wt %, based on the total weight of the composition. Incertain embodiments, the composition further comprises a secondflavoring and/or fragrancing agent. In certain embodiments, the secondflavoring and/or fragrancing agent may be present in an amount of about0.000001% to about 90% by weight, based on the total weight of thecomposition.

In certain embodiments, the composition is an edible composition. Incertain embodiments, the composition is a food or beverage product. Incertain embodiments, the beverage is beer, an alcohol containingbeverage, or other non-alcohol containing beverage product. In certainembodiments, the composition is an inhalation composition. In certainembodiments, the composition is a flavor and/or fragrance composition.

According to a another aspect, provided is for augmenting or enhancingthe gassy aroma or taste of a product, the process comprising the stepof adding to said product an organosulfur compound selected from prenylmercaptan, 2-methylthiophene, 3-methylthiophene, dimethyl disulfide,diprenyl disulfide, 3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, and dimethyl sulfide, or a combination of any two or morethereof, wherein the product is an edible product, an aerosol product, aflavor product, a fragrance product, or an inhalable product. In certainembodiments, the product is an edible product or an inhalable product.In certain embodiments, the edible product is a food or beverageproduct. In certain embodiments, the beverage is beer, any alcoholcontaining beverage, or other non-alcohol containing beverage product.

In certain embodiments, the organosulfur compound is added in an amountof from about 0.000001 wt % to about 0.6 wt %, based on the total weightof the product. In certain embodiments of the fourth aspect, theorganosulfur compound comprises from about 0.000001 wt % to about 0.3 wt% of prenyl mercaptan and from about 0.000001 wt % to about 0.3 wt % of2-methylthiophene. In certain embodiments, the process further comprisesadding a primary terpene compound selected from the group consisting ofmyrcene, β-caryophyllene, limonene, α-pinene, β-pinene, valencene,ocimene, terpinolene, or a combination of any two or more thereof. Incertain embodiments, the primary terpene compound is added in an amountof from about 0.1 wt % to about 99 wt %, based on the total weight ofthe composition.

The foregoing summary is illustrative only and is not intended to be inany way limiting. In addition to the illustrative aspects, embodimentsand features described above, further aspects, embodiments and featureswill become apparent by reference to the following drawings and thedetailed description.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 represents structures of compounds discovered contributing to gasodor in cannabis.

FIG. 2 shows a calibration curve of 1-pentanethiol used to obtainconcentrations of prenyl mercaptan and prenyl thioacetate.

FIG. 3 represents 2-Dimensional chromatograms of the GC x GC-SCD and GCx GC-TOF-MS highlighting prenyl mercaptan and prenyl thioacetate.

FIG. 4 shows mass spectrum of prenyl mercaptan in Bacio Gelato and massspectrum of prenyl mercaptan obtained from the NIST mass spectraldatabase.

FIG. 5 represents 2-Dimensional sulfur chemiluminescence detector(“SCD”) chromatograms of the GC x GC-SCD and GC x GC-TOF-MS comparingprenyl mercaptan elution in Bacio Gelato versus the standard

FIG. 6 shows mass spectrum of prenyl thioacetate in Bacio Gelato and astandard sample, both showing the peak for prenyl thioacetate at¹T_(R)=20.554 minutes and ²T_(R)=3.5943 seconds.

FIG. 7 represents 2-Dimensional sulfur chemiluminescence detector(“SCD”) chromatograms of the GC x GC-SCD and GC x GC-TOF-MS comparingprenyl thioacetate elution in Bacio Gelato versus the standard.

10021)) FIG. 8 represents 1-Dimensional sulfur chemiluminescencedetector (“SCD”) chromatograms of selected strains showing thedifferences in concentration of prenyl mercaptan (˜10.2 minutes) ingassy and non-gassy cultivars.

FIG. 9 represents 1-Dimensional sulfur chemiluminescence detector(“SCD”) chromatograms of selected strains showing the differences inconcentration of prenyl thioacetate (˜10.2 minutes) in gassy andnon-gassy cultivars.

DETAILED DESCRIPTION

Various embodiments are described hereinafter. It should be noted thatthe specific embodiments are not intended as an exhaustive descriptionor as a limitation to the broader aspects discussed herein. One aspectdescribed in conjunction with a particular embodiment is not necessarilylimited to that embodiment and can be practiced with any otherembodiment(s).

As used herein, “about” will be understood by persons of ordinary skillin the art and will vary to some extent depending upon the context inwhich it is used. If there are uses of the term which are not clear topersons of ordinary skill in the art, given the context in which it isused, “about” will mean up to plus or minus 10% of the particular term.

The use of the terms “a” and “an” and “the” and similar referents in thecontext of describing the elements (especially in the context of thefollowing claims) are to be construed to cover both the singular and theplural, unless otherwise indicated herein or clearly contradicted bycontext. Recitation of ranges of values herein are merely intended toserve as a shorthand method of referring individually to each separatevalue falling within the range, unless otherwise indicated herein, andeach separate value is incorporated into the specification as if it wereindividually recited herein. All methods described herein can beperformed in any suitable order unless otherwise indicated herein orotherwise clearly contradicted by context. The use of any and allexamples, or exemplary language (e.g., “such as”) provided herein, isintended merely to better illuminate the embodiments and does not pose alimitation on the scope of the claims unless otherwise stated. Nolanguage in the specification should be construed as indicating anynon-claimed element as essential.

The phrase “and/or,” as used herein in the specification and in theclaims, should be understood to mean “either or both” of the elements soconjoined, i.e., elements that are conjunctively present in some casesand disjunctively present in other cases. Other elements may optionallybe present other than the elements specifically identified by the“and/or” clause, whether related or unrelated to those elementsspecifically identified. As a non-limiting example, a reference to “Xand/or Y” can refer, in one embodiment, to X only (optionally includingelements other than Y); in another embodiment, to Y only (optionallyincluding elements other than X); in yet another embodiment, to both Xand Y (optionally including other elements).

Unless indicated otherwise, reference to “percent” is to be understoodas “weight percent,” and reference to “ratio” is as a weight/weightratio.

As used herein, the term “terpene compound” is understood to mean anyorganic compound that contains at least one isoprene subunit within itsstructure and their oxygenated derivatives.

As used herein, the terms “odor” and “aroma” are used interchangeablyand represent the sensory attributes of certain substances perceptiblydetermined by the olfactory system.

As used herein, the term “flavoring agent” is understood to mean anadditive that is meant to improve the taste or aroma impression of foodor other substances, and can include both natural and syntheticingredients.

As used herein, the term “gassy” is understood to be an organolepticdescriptor that represents a type of Cannabis aroma that emulates asulfurous petroleum odor.

As used herein, the term “strain” is used to represent various chemovarsor cultivars.

As used herein, the term “cultivar” represents a group of similar plantsthat by structural features and performance (i.e., morphological andphysiological characteristics) can be identified from other varietieswithin the same species. Furthermore, the term “cultivar” variouslyrefers to a variety, strain, or race of plant that has been produced byhorticultural or agronomic techniques and is not normally found in wildpopulations. The terms cultivar, variety, strain, and race are oftenused interchangeably by plant breeders, agronomists, and farmers.

As used herein, the term “landrace” is used to represent a local varietyof a domesticated plant species that has developed largely by naturalprocesses, by adaptation to the natural and cultural environment inwhich it lives.

As used herein, the term “plant matter” is used to represent to any partof a plant including but not limited to the flower bud, leaf, petal,flower, stem, seed, embryo, shoot, root, stipule, ovule, bract,trichome, branch, petiole, internode, bark, pubescence, tiller, rhizome,frond, blade, ovule, pollen, stamen, and the like.

As used herein, the term “dry flower” is understood to mean a flower orbud of the plant matter that has been cured and dried and has less thanabout 0.63 water activity, or alternatively about 13% moisture by weightof the flower. Dry flower, or dry herb, is what is used for rolling intoa smokable composition (i.e. a “joint”) or in an edible form, forexample.

In some embodiments the plant matter may be ‘alive’ or ‘wet’ which meansit is not cured. Thus, the contents of various components may bemeasured in terms of dry flow, wet flower, extracts, or otherwise.

Various aspects and/or embodiments of this disclosure relate tocompositions, products, and methods that are capable of, or adapted to,providing, augmenting, or enhancing the gassy odor or aroma. Otheraspects and/or embodiments relate to plant species, cultivars, andmethods of breeding plant species which include compounds capable ofproviding gassy odor or aroma and/or and modifying the olfactoryqualities of the gassy aroma. Yet other aspects and/or embodimentsrelate to methods for analyzing and/or identifying the compounds thatcontribute to a gassy aroma associated with a product.

Provided herein are compositions comprising organosulfur compounds thatare capable of providing a gassy aroma and/or and modifying theolfactory qualities of the gassy aroma. The organosulfur compoundsinclude known organosulfur compounds, such as for example and withoutlimitation, mercaptans, thiols, sulfides, disulfides, polysilfides, andthioesters that contribute to or enhance the desired aroma and/orolfactory qualities of the composition. Suitable organosulfur compounds,include, but are not limited to, prenyl mercaptan, 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, and dimethyl sulfide. In certain embodiments, theorganosulfur compound includes prenyl mercaptan, 2-methylthiophene,3-methylthiophene, or a combination of any two or more thereof. Incertain embodiments, the organosulfur compound includes prenylmercaptan, 2-methylthiophene, prenyl thioacetate or a combination of anytwo or more thereof. In certain embodiments, the organosulfur compoundincludes prenyl mercaptan, 2-methylthiophene, dimethyl disulfide, prenylthioacetate or a combination of any two or more thereof. Any combinationof the organosulfur compounds disclosed here can be included in thecompositions. Structures of illustrative organosulfur compounds thatcontribute to the desirable odor, e.g., gassy odor in cannabis areillustrated in FIG. 1.

In certain embodiments, the organosulfur compounds may be present at upto about 5% by weight of the total composition, up to about 2%, up toabout 1%, up to about 0.6%, up to about 0.3%, up to about 0.2% or up toabout 0.1% by weight of the total weight of the composition. Forexample, the organosulfur compounds are present in the composition fromat least about 0.0000001% by weight of the total composition, at leastabout 0.000001%, at least about 0.00001%, at least about 0.0001%, atleast about 0.001%, at least about 0.01%, at least about 0.05% or atleast about 0.1% by weight. This includes where the organosulfurcompound is present from about 0.0000001% to about 10% of the totalweight of the composition, including without limitation, about 0.00001%to about 5%, about 0.0001% to about 3%, about 0.001% to about 2%, orabout 0.01% to about 1% of the total weight of the composition, about0.0000001% to about 0.5%, about 0.0000001% to about 0.2%, about0.0000001% to about 0.1%, or any range including and/or in-between anytwo of these values. In certain embodiments, the organosulfur compoundis from about 0.000001 wt % to about 0.3 wt % of the total weight of thecomposition.

The composition may include about 0.000001 wt % to about 0.3 wt % of thetotal weight of the composition, of prenyl mercaptan. In certainembodiments, the composition includes about 0.000001 wt % to about 0.3wt % of the total weight of the composition, of 2-methylthiophene. Incertain embodiments, the composition includes about 0.000001 wt % toabout 0.25 wt % of the total weight of the composition, of prenylmercaptan and about 0.000001 wt % to 1.00 wt % of the total weight ofthe composition, of 2-methylthiophene. In certain embodiments, thecomposition includes about 0.000001 wt % to about 0.3 wt % of the totalweight of the composition, of 3-methylthiophene. In certain embodiments,the composition includes about 0.000001 wt % to about 0.3 wt % of thetotal weight of the composition, of dimethyl disulfide. In certainembodiments, the composition includes about 0.000001 wt % to about 0.3wt % of the total weight of the composition, of diprenyl disulfide. Incertain embodiments, the composition includes about 0.000001 wt % toabout 0.3 wt % of the total weight of the composition, of3-methyl-2-buten-1-yl thiolacetate. In certain embodiments, thecomposition includes about 0.000001 wt % to about 0.3 wt % of the totalweight of the composition, of3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene. In certainembodiments, the composition includes about 0.000001 wt % to about 0.3wt % of the total weight of the composition, of prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene). In certain embodiments, thecomposition includes about 0.000001 wt % to about 0.3 wt % of the totalweight of the composition, of prenyl thioacetate. In certainembodiments, the composition includes about 0.000001 wt % to about 0.3wt % of the total weight of the composition, of thiogeraniol. In certainembodiments, the composition includes about 0.000001 wt % to about 0.3wt % of the total weight of the composition, of dimethyl sulfide.Various combinations of organosulfur compounds may also be used in thecompositions. For example, prenyl mercaptan may be combined with otherorganosulfur compounds in suitable amounts to provide the desired gassyaroma profile. Likewise, combinations of other organosulfur compoundsdescribed herein may also be used in the concentration ranges describedherein. Thus, in certain embodiments, the composition includes about0.000001 wt % to about 0.3 wt % of the total weight of the composition,of prenyl mercaptan and 0.000001 wt % to about 0.3 wt % of the totalweight of the composition, of prenyl thioacetate.

In addition to the organosulfur compounds, in certain embodiments, thecompositions may include one or more terpene compounds. Non-limitingexamples of terpene compounds include hemiterpenes, monoterpenes,sesquiterpenes, diterpenes, sesterterpenes, triterpenes,sesquarterpenes, tetraterpenes, polyterpenes, terpenoids andnoriso-prenoids. Suitable terpene compounds may include a primaryterpene compound and a secondary terpene compound. Illustrative primaryand secondary terpene compounds include, but are not limited to,myrcene, β-caryophyllene, α or β-Pinene, α or β-phellandrene, limonene,terpinolene, linalool, pinene, terpineol, fenchyl alcohol, α-bisabolol,camphene, terpinolene, humulene, geraniol, camphor, cedrene, 1-menthol,cis-β-ocimene, trans-β-ocimene, terpinene, delta-3-carene, isoborneol,nerol, valencene, farnesene (t), fenchone, ocimene, bergotamene,thujene, ylangene, sabinene hydrate, and the like, or a combination ofany two or more thereof. Many other terpenes are known in the art andcommercially available, and can be used in the compositions.

In certain embodiments, the primary terpene compounds may include, butare not limited to, myrcene, β-caryophyllene, limonene, α-pinene,β-pinene, valencene, ocimene and terpinolene, and the like, or acombination of any two or more thereof. In certain embodiments, theprimary terpene compounds constitute a major amount of the total terpenecontent or is a major contributor to the resulting aroma of thecomposition. In certain embodiments, the primary terpene compoundsconstitute at least about 5% by weight of the total composition, atleast about 10%, at least about 20%, at least about 30%, at least about40%, at least about 50%, at least about 60%, at least about 70%, atleast about 80% or at least about 90% by weight. In certain embodiments,the primary terpene compounds constitute up to about 99.99% by weight ofthe total composition, up to about 99%, up to about 95%, up to about92%, up to about 90%, up to about 85% or up to about 80% by weight ofthe total weight of the composition. In certain embodiments, the primaryterpene compound constitutes about 5% to about 99.99% of the totalweight of the composition, including without limitation, about 10% toabout 98%, about 20% to about 98%, about 30% to about 98%, about 40% toabout 98%, about 50% to about 95%, about 60% to about 90%, or about 70%to about 85% of the total weight of the composition, or any rangeincluding and/or in-between any two of these values.

In certain embodiments, the primary terpene compound is present in anamount of from about 0.1 wt % to about 90 wt %, based on the totalweight of the composition. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition, of myrcene. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition, of β-caryophyllene. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition, of limonene. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition of α-pinene. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition of (3-pinene. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition of valencene. In certain embodiments, the compositionincludes about 0.1 wt % to about 90 wt % of the total weight of thecomposition of ocimene. In certain embodiments, the composition includesabout 0.1 wt % to about 90 wt % of the total weight of the compositionof terpinolene.

In certain embodiments, the compositions include a secondary terpenecompound. In certain embodiments, the secondary terpene compounds mayinclude, but are not limited to, humulene, linalool, α-bisabolol, nerol,α-phellandrene, α-terpineol, farnesene, fenchyl alcohol, geraniol,menthol, citronellol, citronellal, geranyl acetate, nerolidol, citral,and the like, or a combination of any two or more thereof. In certainembodiments, the secondary terpene compounds constitute a minor amountof the total terpene content or is a minor contributor to the resultingaroma of the composition. In certain embodiments, the secondary terpenecompounds constitute up to about 30% by weight of the total composition,up to about 20%, up to about 10%, up to about 5%, up to about 2%, up toabout 1% or up to about 0.1% by weight of the total weight of thecomposition. In certain embodiments, the secondary terpene compoundsconstitute at least about 0.0001% by weight of the total composition, atleast about 0.001%, at least about 0.01%, at least about 0.1%, at leastabout 0.5%, at least about 1% or at least about 2% by weight. In certainembodiments, the secondary terpene compound constitutes about 0.0001% toabout 30% of the total weight of the composition, including withoutlimitation, about 0.001% to about 25%, about 0.1% to about 20%, about 1%to about 10%, or about 2% to about 5% of the total weight of thecomposition, or any range including and/or in-between any two of thesevalues. In certain embodiments, the secondary terpene compound ispresent in an amount of from about 0.01 wt % to about 10 wt %, based onthe total weight of the composition

In certain embodiments, the secondary terpene compound is present in anamount of from about 0.1 wt % to about 30 wt %, based on the totalweight of the composition. In certain embodiments, the compositionincludes about 0.1 wt % to about 30 wt % of the total weight of thecomposition, of one or more secondary terpenes selected from humulene,linalool, α-bisabolol, nerol, α-phellandrene, α-terpineol, farnesene,fenchyl alcohol, geraniol, menthol, citronellol, citronellal, geranylacetate, nerolidol and citral.

In certain embodiments, the composition includes about 0.000001 wt % toabout 0.3 wt % of prenyl mercaptan and about 0.1 wt % to 90 wt %myrcene, based on the total weight of the composition. In certainembodiments, the composition includes about 0.000001 wt % to about 0.3wt % of prenyl mercaptan, about 0.1 wt % to 90 wt % myrcene, and about0.1 wt % to 90 wt % D-limonene, based on the total weight of thecomposition. In certain embodiments, the composition includes about0.000001 wt % to about 0.3 wt % of prenyl mercaptan, about 0.1 wt % to90 wt % myrcene, about 0.1 wt % to 90 wt % of D-limonene, and about 0.1wt % to 90 wt % of β-Caryophyllene based on the total weight of thecomposition. In certain embodiments, the composition includes about0.000001 wt % to about 0.3 wt % of prenyl mercaptan, about 0.000001 wt %to about 0.3 wt % of 2-methylthiophene, about 0.1 wt % to 90 wt %myrcene, about 0.1 wt % to 90 wt % of D-limonene, and about 0.1 wt % to90 wt % of β-Caryophyllene based on the total weight of the composition.

In another aspect, the composition can be formulated to have variousapplications. In a non-limiting way, the composition can be an ediblecomposition, an aerosol composition, a flavor composition, a fragrancecomposition, or an inhalable composition. In certain embodiments, anedible product comprising a composition described herein is provided. Incertain embodiments, the composition is an edible composition. Incertain embodiments, the composition is an aerosol composition. Incertain embodiments, the composition is a flavor composition. In certainembodiments, the composition is a fragrance composition. In certainembodiments, the composition is an inhalable composition.

The compositions may further include suitable second flavoring and/orfragrancing agents including, but not limited to, ethyl butyrate, ethylisovalerate, methyl anthranillate, vanillin, ethyl maltol, maltol,strawberry furanone (4-OH-2,5-dimethyl-3-furanone), raspberry ketone(anisyl acetone), isoamyl acetate, isoamyl butyrate, ethyl caproate,octanal, octanol, aldehyde c-16, allyl caproate, ortho-tolualdehyde,benzaldehyde, sweet almond oil, bitter almond oil, beta-ionone, hexylbutyrate, hexyl acetate, hexyl hexanoate, propyl caproate, folione,citronellyl formate, 2-phenylpropyl isobutyrate, propionyl thiazole,methional, methyl heptadienone, gamma decalactone, melonal, passifloran,methyl-2 butyl acetate, lime terpenes, peppermint oil, orange oil, andthe like, or a combination of any two or more thereof. Additionalexamples of flavoring agents include ingredients that are “generallyrecognized as safe” (“GRAS”) by the United States Food and DrugAdministration (“FDA”), for example, those listed as approved under 21C.F.R. §§ 172.510, 172.515, and 172.560.

In certain embodiments, the second flavoring and/or fragrancing agents,when present, constitutes about 0.000001% to about 90% by weight of thetotal weight of the composition, including without limitation, about0.000001% to about 80%, about 0.000001% to about 70%, about 0.000001% toabout 60%, about 0.000001% to about 50%, about 0.000001% to about 40%,about 0.000001% to about 30%, about 0.000001% to about 20%, about0.00001% to about 15%, about 0.0001% to about 10%, about 0.001% to about8%, about 0.01% to about 5%, about 0.1% to about 3%, or about 1% toabout 2% by weight of the total weight of the composition, or any rangeincluding and/or in-between any two of these values.

Depending upon the end application, the compositions may include otheringredients, such as surfactants, co-solvents, propellants, otherflavoring agents, medicinal agents, perfumes, stabilizers, thickeners,binders, preservatives, emulsifiers, essential oils, water, salt,sweeteners, gelatin, food additives, colorants, excipients, diluents,and the like or a combination of any two or more thereof.

The organosulfur compounds described herein may be used in any flavorand fragrance applications. Accordingly, in one aspect, provided hereinare flavor and fragrance compositions comprising organosulfur compoundsincluding, but not limited to, prenyl mercaptan, 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, dimethyl sulfide; and a terpene compound. In certainembodiments, the organosulfur compound includes prenyl mercaptan,2-methylthiophene, 3-methylthiophene, or a combination of any two ormore thereof.

In certain embodiments, the compositions may further include acannabinoid active agent. The cannabinoid active agent may be selectedfrom any of the known cannabinoids, including, without limitation,tetrahydrocanabinols, tetrahydrocannabinolic acids, cannabidiol,cannabidiolic acid, cannabigerolic acid, cannabigerol,cannabigerovarinic acid, cannabigerolovarin, cannabichromenic acid,cannabichromene, cannabidivarin, cannabidivarinic acid, cannabivarin,cannabivarinic acid, tetrahydrocannabivarinic acid,tetrahydrocannabivarin, cannabinolic acid, cannabinol, cannabinodiol,cannabielsoin, cannabicyclol, and cannabicitran and isomers thereof, ora combination of any two or more thereof. When used, the cannabinoidactive agent is present in an amount of from about 0.05% to 99.9% by wtbased on the total weight of composition, including from 0.1 to 45%, 1to 40%, 2 to 35%, 5 to 30%, or 10 to 20% by wt, based on the totalweight of the composition.

The compositions described herein may be used in a variety of productsincluding edible products, aerosol products, fragrance products, flavorproducts, inhalable products, consumer products, personal care products,and household products. The organosulfur compound-containingcompositions containing one or more organosulfur compounds maysynergistically enhance the olfactory effects of products to closelyemulate cannabis aroma and/or flavor. In certain embodiments, theorganosulfur compound-containing compositions can be used as an additiveto synergistically enhance the aroma and/or flavor of products such asedible products, aerosol products, fragrance products, flavor products,inhalable products, consumer products, personal care products, andhousehold products. In certain embodiments, the edible product is a foodproduct or a beverage product.

In another aspect, the present technology relates to various productsthat may include the organosulfur compound-containing compositionsdescribed herein. Illustrative products include, but are not limited toedible products, aerosol products, fragrance products, flavor products,or inhalable products. In certain embodiments, an edible productcomprising a composition described herein is provided. In certainembodiments, the edible product is a food or beverage product. Incertain embodiments, the beverage is beer, any alcohol containingbeverage, or other non-alcohol containing beverage product. In certainembodiments, a flavor and fragrance product comprising a compositiondescribed herein is provided. In certain embodiments, an inhalationproduct comprising the composition described herein is provided. Incertain embodiments, the inhalation product is a vaping composition. Incertain embodiments, a flavor and/or fragrance delivery systemcomprising the composition described herein is provided.

In another aspect, an edible product or an inhalation product comprisesa composition comprising an organosulfur compound selected from thegroup consisting of prenyl mercaptan, 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, and dimethyl sulfide. In certain embodiments, thecomposition comprise from about 0.000001 wt % to about 0.3 wt % ofprenyl mercaptan, based on the total weight of the composition. Incertain embodiments, the composition comprises from about 0.000001 wt %to about 0.3 wt % of 2-methylthiophene, based on the total weight of thecomposition. In certain embodiments, the edible product is a food orbeverage product.

Other aspects of the present technology relate to Cannabis plants. TheCannabis plant may be a hybrid plant or an engineered plant, and can beproduced via known methods such as seed production or asexualreproduction. In some embodiments, provided is a cannabis plant, or anasexual clone thereof, or a plant part, tissue, or cell thereofcomprising an organosulfur compound content greater than 0.00001 μg/mgas measured by gas chromatography coupled with a sulfurchemiluminescence detector and calculated based on dry weight of thedried, ground flower. The gas chromatography can be one-dimensional or atwo-dimensional gas chromatography coupled with a sulfurchemiluminescence detector (GCxGC-SCD). In some embodiments,organosulfur compound content is greater than about 0.00001 μg/mg,greater than about 0.0002 μg/mg, greater than about 0.0005 μg/mg,greater than about 0.0007 μg/mg, greater than about 0.001 μg/mg %,greater than about 0.005 μg/mg, or greater than about 0.01 μg/mg asmeasured by gas chromatography coupled with a sulfur chemiluminescencedetector and calculated based on dry weight of the dried, groundcannabis flower. In some embodiments, organosulfur compound content isless than about 0.1 μg/mg as measured by gas chromatography coupled witha sulfur chemiluminescence detector and calculated based on dry weightof the dried, ground flower In some embodiments, organosulfur compoundcontent is less than about 0.05 μg/mg, less than about 0.01 μg/mg, lessthan about 0.005 μg/mg, less than about 0.003 μg/mg, greater than about0.002 μg/mg, or greater than about 0.001 μg/mg as measured by gaschromatography coupled with a sulfur chemiluminescence detector andcalculated based on dry weight of the dried, ground cannabis flower.

Methods for analyzing and/or identifying the compounds that contributeto a gassy aroma associated with a product, e.g., a cannabis product,are also provided herein. The methods include analyzing the constituentsof a product having a gassy aroma using various devices and methodsincluding, but not limited to, gas chromatography/time-of-flightmass-spectrometer (GC/TOF-MS), two-dimensional gas chromatography-timeof flight mass spectrometry (2DGC-TOF MS), flame ionization detector(HD), sulfur chemiluminescence detector (SCD), gas chromatography/massspectrometry (GC/MS), gas chromatography with atomic emission detector(GC/AED), gas chromatography/flame ionization detection/olfactometry(GC/FID/olfactometry) or high performance liquid chromatography (HPLC),or a combination of any two or more thereof.

Cannabis strains and compositions with varying degrees of gassy aromamay be analyzed using 2-dimensional gas chromatography equipped with atime-of-flight mass-spectrometer (TOF-MS), flame ionization detector(FID), and a sulfur chemiluminescence detector (SCD). It has now beensurprisingly and unexpectedly discovered that a correlation existsbetween the organoleptic response, i.e. how ‘gassy’ a given strainsmells to the human nose, and the concentration of certain organosulfurcompounds. Such organosulfur compounds may include, but are not limitedto, prenyl mercaptan (3-methylbut-2-ene-1-thiol), 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate, thiogeraniol((E)-3,7-dimethyl-2,6-octadien-1-thiol), and dimethyl sulfide. It wasdiscovered that the odors of these organosulfur compounds coupled withterpene compounds present in a strain may yield the particular ‘flavor’of the gas present. Although low in relative concentration compared tothe terpenes, the organosulfur compounds were found to have asignificant impact on aroma and flavor. The methods for identificationand analysis of the odor-producing compounds described herein canadvantageously be used to guide cultivators for targeting and producingplants, clones, or plant cells with or without specific aromasassociated with them, as well as develop formulations of food andbeverages when targeting a unique gassy aroma or odor.

One aspect of the present technology relates to a method for detectingsulfur-containing compounds in a cannabis plant by analyzing theheadspace gas from a cannabis sample using a gas chromatography. The gaschromatography can be a one- or two-dimensional gas chromatographcoupled a sulfur chemiluminescence detector (SCD). The SCD can be usedin conjugation with other detectors such as a flame ionization detector(FID), a mass spectrometer (MS), nitrogen chemiluminescence detector(NCD), a nitrogen phosphorus detector (NPD), an atomic emission detector(AED), a flame photometric detector (FPD), or an electron capturedetector (ECD). Suitable samples of the cannabis plant material can beplaced in a bottle and the gases in a headspace bottle, can be collectedusing headspace tools and injected into a gas chromatography-sulfurchemiluminescence detector combined device, using an inert gas such asnitrogen as carrier gas for the gas chromatography, and performingqualitative and quantitative detection through a sulfurchemiluminescence detector. The cannabis samples can be incubated andagitated at suitable temperature (e.g., 40-150° C.) prior to collectionof the headspace gas sample. In some embodiments, the cannabis samplemay include cannabis flower material, such as dried flower, dried, andground flower, a wet flower, or a flower extract. In some embodiments,the flower material may be cured. In some embodiments, the flowermaterial may be uncured.

Instrument parameters that can be used in a 2-dimensional gaschromatographic system include using a BPX5 (5% PhenylPolysilphenylene-siloxane) first dimension column and a high polarityMEGA-WAX (Polyethylene glycol (PEG)) secondary column.

A suitable instrument temperature ramp method may include: an initialtemperature of 45° C., the temperature is maintained for 5 min, thetemperature is increased to 90° C. at the speed of 5° C./min, then thetemperature is increased to 130° C. at the speed of 2° C./min, thetemperature is increased to 240° C. at the speed of 5° C./min, and thetemperature is maintained for 1 min;

Suitable instrument parameters include:

sample inlet temperature: 200° C.;

SCD plasma Burner temperature: 800° C.;

SCD Base temperature: 250° C.;

Oxidizer flow (O₂): 11.50 mL/min,

Upper H₂ flow: 38.00 mL/min; and

Upper H₂ flow: 8.00 mL/min.

Illustrative sulfur-containing compounds which may be detected oridentified using the gas chromatography-sulfur chemiluminescencedetector method, may include, but are not limited to, prenyl mercaptan(3-methylbut-2-ene-1-thiol), 2-methylthiophene, 3-methylthiophene,dimethyl disulfide, diprenyl disulfide, 3-methyl-2-buten-1-ylthiolacetate, 3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene,prenylmethylthiol (1-(methylsulfanyl)-3-methyl-2-butene), prenylthioacetate, thiogeraniol ((E)-3,7-dimethyl-2,6-octadien-1-thiol), anddimethyl sulfide.

Another aspect of the present technology relates to a process foraugmenting or enhancing the gassy aroma or taste of a product by addingto the product an organosulfur compound selected from prenyl mercaptan,2-methylthiophene, 3-methylthiophene, dimethyl disulfide, diprenyldisulfide, 3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, dimethyl sulfide, or a combination of any two or morethereof. The organosulfur compound may be added in amounts as describedherein, for example from about 0.000001 wt % to about 10 wt %, fromabout 0.000001 wt % to about 0.6 wt %, or from about 0.000001 wt % toabout 3 wt %, based on the total weight of the product. In certainembodiments, the process includes adding from about 0.000001 wt % toabout 0.3 wt % of prenyl mercaptan and from about 0.000001 wt % to about0.3 wt % of 2-methylthiophene to the product.

In certain embodiments, the process further includes adding a terpenecompound to the product. Suitable terpene compounds may include theprimary and secondary terpene compounds described herein. In certainembodiments, the primary terpene compound is selected from the groupconsisting of myrcene, β-caryophyllene, limonene, α-pinene, β-pinene,valencene, ocimene, and terpinolene. In certain embodiments, thesecondary terpene compound is selected from the group consisting ofhumulene, linalool, α-bisabolol, nerol, α-phellandrene, α-terpineol,farnesene, fenchyl alcohol, geraniol, menthol, citronellol, citronellal,geranyl acetate, nerolidol, and citral. In certain embodiments, theprimary terpene compound is added in an amount of from about 0.1 wt % toabout 90 wt %, based on the total weight of the product. In certainembodiments, the secondary terpene compound is added in an amount offrom about 0.01 wt % to about 10 wt %, based on the total weight of thecomposition.

In certain embodiments, provided herein is a process for augmenting orenhancing the gassy aroma or taste of a product selected from an edibleproduct, an aerosol product, a fragrance product, a flavor product, andan inhalable product. The augmenting or enhancing may include adding tothe product an organosulfur compound selected from prenyl mercaptan,2-methylthiophene, 3-methylthiophene, dimethyl disulfide, diprenyldisulfide, 3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, and dimethyl sulfide, or a combination of any two or morethereof. In certain embodiments, the edible product produced by theprocess is provided. In certain embodiments, the edible product is afood or beverage product. In certain embodiments, the beverage is beer,any alcohol-containing beverage, or other non-alcohol containingbeverage product. In certain embodiments, the method for enhancing gassyaroma in a flavor or fragrance composition includes adding to the flavoror fragrance composition, an organosulfur compound selected from prenylmercaptan, 2-methylthiophene, 3-methylthiophene, dimethyl disulfide,diprenyl disulfide, 3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, and dimethyl sulfide, or combination of any two or morethereof.

Yet another aspect of the present technology relates to a method ofproducing a proven gassy aroma composition comprising mixing a terpenecompound with an organosulfur compound selected from the groupconsisting of prenyl mercaptan, 2-methylthiophene and 3-methylthiophene,dimethyl disulfide, diprenyl disulfide, 3-methyl-2-buten-1-ylthiolacetate, 3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene,prenylmethylthiol (1-(methyl sulfanyl)-3-methyl-2-butene), prenylthioacetate, thiogeraniol, and dimethyl sulfide. Suitable terpenecompounds may include the primary and secondary terpene compoundsdescribed herein. In certain embodiments, the primary terpene compoundis selected from the group consisting of myrcene, β-caryophyllene,limonene, α-pinene, β-pinene, valencene, ocimene, and terpinolene. Incertain embodiments, the secondary terpene compound selected from thegroup consisting of humulene, linalool, α-bisabolol, nerol,α-phellandrene, α-terpineol, farnesene, fenchyl alcohol, geraniol,menthol, citronellol, citronellal, geranyl acetate, nerolidol, andcitral.

Aspects of the present technology relate to methods of breeding acannabis plant, wherein the plant produces altered or non-naturalamounts of one or more organosulfur compounds. In one embodiment,provided is a method for breeding an engineered plant, wherein saidcannabis plant comprises one or more organosulfur compound, wherein theengineered cannabis plant produced greater amounts of the organosulfurcompound when compared to the amount of organosulfur compound in anon-engineered or natural plant. Suitable organosulfur compoundsinclude, but are not limited to, prenyl mercaptan, 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, dimethyl sulfide, or a combination of any two or morethereof. In addition to the organosulfur compound plant may also includecannabinoid active agent and a terpene compound. Suitable terpenecompounds include, but are not limited to, myrcene, β-caryophyllene, αor β-Pinene, α or β-phellandrene, limonene, terpinolene, linalool,pinene, terpineol, fenchyl alcohol, α-bisabolol, camphene, terpinolene,humulene, geraniol, camphor, cedrene, 1-menthol, cis-β-ocimene,trans-β-ocimene, terpinene, delta-3-carene, isoborneol, nerol,valencene, farnesene (t), fenchone, ocimene, bergotamene, thujene,ylangene, sabinene hydrate, and the like, or a combination of any two ormore thereof.

Other aspects of the present technology relate to methods for producingan organosulfur compound, wherein said method comprises cultivating aplant, wherein said plant produces an organosulfur compound selectedfrom the group consisting of prenyl mercaptan, 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, dimethyl sulfide or a combination of any two or morethereof. In various embodiments, the prenyl mercaptan is produced at aconcentration of from about 0.000001 wt %-10 wt %. In variousembodiments, the 2-methylthiophene is produced at a concentration offrom about 0.000001%-10%.

Yet other aspects of the present technology relate to method ofproducing a cannabis plant comprising: (i) obtaining a cannabis seed,cutting, or a plant cell, from a cannabis plant, or a clone of saidcannabis plant; (ii) placing said cannabis seed, cutting, or plant cellin an environment conducive to growth; and (iii) allowing said cannabisseed, cutting, or plant cell to produce a cannabis plant, wherein theproduced cannabis plant produces an altered concentration of anorganosulfur compound. For example, the method may produce an engineeredcannabis plant that produces greater amounts of the organosulfurcompound when compared to the amount of organosulfur compound in anon-engineered or natural cannabis plant. The cannabis plant may producean organosulfur compound content of greater than about 0.00001 μg/mg asmeasured by one- or two-dimensional gas chromatograph coupled with asulfur chemiluminscence detector (GCxGC-SCD) and calculated based on dryweight of the dried, ground flower.

In certain embodiments, the engineered cannabis plant may produce one ormore organosulfur compound at a concentration of from about0.000001%-0.5%. Suitable organosulfur compounds include, but are notlimited to, prenyl mercaptan, 2-methylthiophene, 3-methylthiophene,dimethyl disulfide, diprenyl disulfide, 3-methyl-2-buten-1-ylthiolacetate, 3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene,prenylmethylthiol (1-(methylsulfanyl)-3-methyl-2-butene), prenylthioacetate, thiogeraniol, dimethyl sulfide, or a combination of any twoor more thereof. In certain embodiments, the engineered cannabis plantmay produce prenyl mercaptan at a concentration of from about0.000001%-0.5%. In certain embodiments, the engineered cannabis plantmay produce prenyl thioacetate at a concentration of from about0.000001%-0.5%. The produced cannabis plant may include one or more of acannabinoid active agent and a terpene compound.

The organosulfur compounds and terpenes described herein may becommercially sourced or can be readily prepared in a laboratory. Forexample, of diprenyl disulfide can be prepared via S—S coupling fromprenyl mercaptan using the following synthetic scheme:

The reaction maybe conducted using e.g., 2% iodine solution and about2.4% aqueous sodium iodine solution in ethanol or in an organic solventmiscible with water. Diprenyl disulfide may also form in-situ in acomposition containing prenyl mercaptan.

The present invention, thus generally described, will be understood morereadily by reference to the following examples, which are provided byway of illustration and are not intended to be limiting of the presentinvention.

EXAMPLES

Various embodiments will be further clarified by the following examples,which are in no way intended to limit this disclosure thereto.

Example 1: Curation of Cannabis Samples

Samples of cannabis flowers were curated from different sources. Allsamples were stored in clear, colorless scintillation vials in a −20° C.freezer to ensure minimal loss of volatiles and decrease thermaldecomposition. All samples were dried and cured prior to procurement.

Example 2: Sample Preparation

200 mg of each curated flower sample from Example 1 was transferred to2DGC vials followed by mechanically grinding with a spatula. Vial capswere then crimped onto each vial.

Example 3: Characterization and Testing of Cultivars

Twelve cannabis cultivars were analyzed using 2-dimensional gaschromatography, mass spectrometry, and sulfur chemiluminescence todetermine the chemical origin of the gassy odor in cannabis. GC x GCanalysis was performed using the INSIGHT reverse fill flush flowmodulator (Sepsolve Analytical) in conjunction with a 7890B GC (Agilenttechnologies) and BenchTOF TOF-MS (Markes International). Detection andquantification of sulfur-bearing compounds was performed using anAgilent 8355 sulfur chemiluminescence detector (SCD). Sampleintroduction was performed using the Centri sample preparation platform(Markes International).

Samples were incubated and agitated at a temperature of 45° C. for 10minutes, followed by six 1 mL headspace injections from the sample vialto a cryogen free cold trap held at 25° C. After the six injections werecomplete, the cold trap was rapidly heated to 300° C. to desorb thesample in a narrow band onto the analytical columns. The GC x GC columnconfiguration was a polar to apolar setup. The GC oven ramp rates usedwere as follows: The oven was initially set to 45° C. and held for 3minutes. The oven was then ramped at a rate of 5° C. per minute to 90°C., followed a 2.0° C. ramp rate to 130° C., followed last by a 5° C.ramp rate to 240° C. The modulation period set for the flow modulatorwas 7.2 seconds.

Data was collected, integrated, and analyzed using the ChromSpacesoftware platform (Sepsolve Analytical). A 5-point calibration curve wascalculated using 1-Pentanethiol (DCG Partnership I, LTD) to quantify thecompounds detected from the SCD. The solutions were prepared usingserial dilution of the analytical standard with pentane. As sulfur atomsprovide an equimolar response to the amount present in the SCD, anyanalytes containing sulfur were quantified using the 1-Pentanethiolstandard calibration curve. The calibration curve showing detectorresponse versus mass is shown in FIG. 2.

Table 1 summarizes value masses used for each calibration point and themeasured SCD peak volume.

TABLE 1 Calibration Mass of SCD point analyte (μg) peak volume 18.420E−02 1.967E+09 2 4.210E−02 1.026E+09 3 2.105E−02 5.502E+08 44.210E−03 5.485E+07 5 2.105E−04 3.759E+06

The cultivars were chosen with varying degrees of gassy aroma todetermine the chemical origin. A clear correlation was observed betweenconcentration of prenyl mercaptan and prenyl thioacetate (chemicalstructures shown in FIG. 1) in the SCD data.

Five cannabis fragrance and aroma experts were asked to rate the odorsof each strain using a blind olfactory test. Table 2 summarizes thecultivars, concentrations of compounds of interest, and the organolepticresponse of each flower.

TABLE 2 Concentration Concentration of Prenyl of Prenyl Prenyl Prenylmercaptan in thioacetate in mercaptan thioacetate Mass of dry flower dryflower Organoleptic Cultivar mass (μg) mass (μg) flower (mg) (μg/mg)(μg/mg) response Bacio 0.2433 0.0014 200 1.46E−03 8.49E−06 High GasGelato SFV OG 0.0051 0.0016 202 3.01E−05 9.74E−06 Moderate Gas Yeti OG0.1007 0.0042 201 6.00E−04 2.52E−05 High Gas OG Kush 0.0384 0.0022 2012.29E−04 1.33E−05 High Gas Marathon 0.0059 0.0003 200 3.51E−05 1.67E−06Moderate Gas OG Jack Not detected Not detected Not detected Not detectedNot detected No Gas Herer Landrace Not detected Not detected Notdetected Not detected Not detected No Gas sample 1 Landrace Not detectedNot detected Not detected Not detected Not detected No Gas sample 2Landrace Not detected Not detected Not detected Not detected Notdetected No Gas sample 3 Landrace Not detected Not detected Not detectedNot detected Not detected No Gas sample 4

Of all cultivars, Bacio Gelato was found to possess the highestconcentration of prenyl mercaptan as shown in Table 2. This highconcentration results in an intense, piercing, gassy aroma. Prenylthioacetate is also present in the sample, which further contributes tothe aroma of this cultivar. FIG. 3 shows the 2-dimensional chromatogramsfor the GC x GC-SCD and GC x GC-TOF-MS data. Prenyl mercaptan elutes at¹T_(R)=10.082 minutes and ²T_(R)=2.313 seconds while prenyl thioacetateelutes at ¹T_(R)=20.554 minutes and ²T_(R)=3.5943 seconds. Prenylthioacetate has a higher second dimension retention time due to the morepolar nature of the compound imparted by the acetate group. The chemicalidentities of the compounds of interest were determined by analyzingtheir mass spectral data. As prenyl mercaptan has a molar mass of 102.20g/mol, the mass spectral peak at m/z˜102 corresponds to the molecularion. The major peak located at m/z˜69 most likely corresponds to theprenyl ion C₅H₁₀ ⁺. This is further substantiated as prenyl thioacetatealso has an intense peak located at m/z˜69, which also has the prenylfunctional group. The final major peak is located at m/z˜41, which mostlikely corresponds to the C₃H₆ ⁺ fragment. The spectrum obtain from theexperimental data was then compared with that provided by the NISTSpectral Library v17 (2017), and Wiley Registry of Mass Spectra (11^(th)Edition) which showed excellent match with prenyl mercaptan (FIG. 4).Lastly, data on a prenyl mercaptan standard (Excellentia, 1% intriacetin) confirmed the elution retention times in the 2-dimensionaldata (FIG. 5). The aroma of the prenyl mercaptan standard was extremelypungent even at 1% concentration in triacetin indicating a very lowolfactory response. A 10-fold dilution was conducted which resulted in asimilar aroma to that in the Bacio Gelato flower, further confirming theimportance of prenyl mercaptan towards the gassy aroma.

Example 4: Identification of Other Aroma Compounds

A second eluent of interest in the SCD data suggested a compound withsimilar functionality based on the mass spectral data (FIG. 6). Theeluent with retention times of ¹T_(R)=20.554 minutes and ²T_(R)=3.5943seconds contains the same major ions m/z=41, 69 and 102, indicating theprenyl functionality most likely exists in this compound as well as themolecular fragment C₅H₁₀S^(±). However, the largest m/z ratio is locatedat ˜144, suggesting a larger compound with more functionality thanprenyl mercaptan. Additionally, the higher second dimension retentiontime than prenyl mercaptan (3.5943 and 2.313 seconds, respectively)indicates greater polarity and presence of electronegative atoms such asoxygen. Based on the mass spectral data and the location in the2-dimensional chromatograms, the formula was indicated to be C₇H₁₂OS,which would yield the structure of 3-methyl-2-butenyl acetothioate, orprenyl thioacetate (CAS #33049-93-3). A comparison with a standardsample of prenyl thioacetate (Toronto Research Chemicals, 97%) indicatedthat the major eluent appears at the same retention times as the unknownin Bacio Gelato (FIG. 7), confirming that the unknown in gassy cannabissamples is prenyl thioacetate. The aroma of the prenyl thioacetatestandard was observed to be similar to prenyl mercaptan but had aslightly sharper scent, confirming that this compound also contributesto the gassy aroma in cannabis.

The remaining cultivars were screened for the presence of prenylthioacetate and their respective concentrations as shown in Table 2.FIG. 8 shows the SCD 1-D chromatograms of the 2-dimensional data toillustrate the differences in prenyl mercaptan in high-gas and low-gassamples. A clear trend was observed such that cultivars with a gassyaroma have detectable peaks, and therefore higher concentrations, ofprenyl mercaptan. A similar trend was also established for prenylthioacetate, where the compound was present in cultivars with a gassyaroma (FIG. 9). Cultivars that had no detectable concentrations of thesecompounds had no appreciable gassy aroma.

These results confirm the origins of the gassy odor in cannabis andexplain how the aroma can be modulated through coupling of othercompounds present in the cannabis plant.

Example 5: Preparation and Testing of Blends

The following blend compositions, namely, Composition A, Composition B,Composition C and Composition D, and were prepared for their prenylmercaptan and 2-methylthiphene content as well as other components. Thecompositions are summarized in Table 3.

TABLE 3 Composi- Composi- Composi- Composi- Compound (wt %) tion A tionB tion C tion D prenyl mercaptan 0.076 0.0454 0.031 0.045 triacetin7.324 4.386 3.04 4.386 2-methylthiophene 0.002 0.0012 0.033 0.001 (1% inD-limonene) Dimethyl Disulfide 0.002 0.0014 — 0.001 (1% in D-limonene)D-Limonene 27.903 24.086 22.64 24.115 Myrcene 22.012 20.88 59.66 20.946β-Caryophyllene 18.985 16.99 2.38 17.846 Linalool 6.292 5.39 2.27 5.665β-Pinene 5.05 4.94 1.74 5.19 Alpha-Terpineol 2.686 2.34 0.35 2.46Alpha-Pinene 2.557 3.19 3.12 3.348 Fenchyl Alcohol 2.465 5.46 0.58 5.733Alpha-Bisabolol 1.775 1.6 0.02 1.676 Camphene 0.754 0.66 1.37 0.692Terpinolene 0.699 2.2 0.49 2.31 Alpha-Humulene 0.313 2.33 0.57 —Geraniol 0.294 0.26 0.0031 0.277 Camphor 0.258 1.18 0.0027 1.24Alpha-Cedrene 0.166 0.16 0.0017 — L-Menthol 0.074 0.07 0.0008 0.078Cis-ocimene 0.055 0.06 0.0006 — Sabinene Hydrate 0.055 0.06 0.0006 0.064Trans-ocimene 0.055 0.33 0.0006 0.403 Alpha-Phellandrene 0.037 0.110.0004 0.114 Alpha-Terpinene 0.037 0.08 0.15 0.081 Delta-3-Carene 0.0372.97 0.0004 3.115 Isoborneol 0.037 0.04 0.0004 0.041 Nerol — 0.01 —0.002 Valencene — 0.04 0.22 0.042 Farnesene (t) — 0.13 0.12 0.134Fenchone — — 0.17 — Ethyl Isobutyrate — — 0.003 — Hexanal — — 0.016 —Hexyl Caproate — — 0.04 — 2-Heptanone — — 0.01 — n-Hexyl butanoate — —0.01 — Pyrazine, — — 0.01 — 2,5-dimethyl- Ylang — — 0.56 — Alpha-methyl— — 0.11 — butanal Bergotamene — — 0.086 — Ocimene — — 0.067 —Alpha-Thujene — — 0.06 — 1-Hexanol — — 0.057 — DiPrenyl DiSulfide — —0.052 — Prenyl Thioacetate — — 0.027 —

Unless otherwise expressly stated, it is in no way intended that anymethod set forth herein be construed as requiring that its steps beperformed in a specific order, nor that with any apparatus specificorientations be required. Accordingly, where a method claim does notactually recite an order to be followed by its steps, or that anyapparatus claim does not actually recite an order or orientation toindividual components, or it is not otherwise specifically stated in theclaims or description that the steps are to be limited to a specificorder, or that a specific order or orientation to components of anapparatus is not recited, it is in no way intended that an order ororientation be inferred, in any respect. This holds for any possiblenon-express basis for interpretation, including: matters of logic withrespect to arrangement of steps, operational flow, order of components,or orientation of components; plain meaning derived from grammaticalorganization or punctuation, and; the number or type of embodimentsdescribed in the specification.

All disclosed ranges are to be understood to encompass and providesupport for claims that recite any and all subranges or any and allindividual values subsumed by each range. For example, a stated range of1 to 10 should be considered to include and provide support for claimsthat recite any and all subranges or individual values that are betweenand/or inclusive of the minimum value of 1 and the maximum value of 10;that is, all subranges beginning with a minimum value of 1 or more andending with a maximum value of 10 or less (e.g., 5.5 to 10, 2.34 to3.56, and so forth) or any values from 1 to 10 (e.g., 3, 5.8, 9.9994,and so forth). Any listed range may be easily recognized as sufficientlydescribing and enabling the same range being broken down into at leastequal halves, thirds, quarters, fifths, tenths, etc. As a non-limitingexample, each range discussed herein may be readily broken down into alower third, middle third and upper third, etc. As will also beunderstood by one skilled in the art all language such as “up to,” “atleast,” “greater than,” “less than,” and the like, include the numberrecited and refer to ranges which may be subsequently broken down intosubranges as discussed above. Finally, as will be understood by oneskilled in the art, a range includes each individual member. Thus, forexample, a group having 1-3 layers refers to groups having 1, 2, or 3layers. Similarly, a group having 1-5 layers refers to groups having 1,2, 3, 4, or 5 layers, and so forth.

The drawings shall be interpreted as illustrating one or moreembodiments that are drawn to scale and/or one or more embodiments thatare not drawn to scale. This means the drawings may be interpreted, forexample, as showing: (a) everything drawn to scale, (b) nothing drawn toscale, or (c) one or more features drawn to scale and one or morefeatures not drawn to scale. Accordingly, the drawings can serve toprovide support to recite the sizes, proportions, and/or otherdimensions of any of the illustrated features either alone or relativeto each other. Furthermore, all such sizes, proportions, and/or otherdimensions are to be understood as being variable from 0-100% in eitherdirection and thus provide support for claims that recite such values orany and all ranges or subranges that may be formed by such values.

The terms recited in the claims should be given their ordinary andcustomary meaning as determined by reference to relevant entries inwidely used general dictionaries and/or relevant technical dictionaries,commonly understood meanings by those in the art, etc., with theunderstanding that the broadest meaning imparted by any one orcombination of these sources should be given to the claim terms (e.g.,two or more relevant dictionary entries should be combined to providethe broadest meaning of the combination of entries, etc.) subject onlyto the following exceptions: (a) if a term is used in a manner that ismore expansive than its ordinary and customary meaning, the term shouldbe given its ordinary and customary meaning plus the additionalexpansive meaning, or (b) if a term has been explicitly defined to havea different meaning by reciting the term followed by the phrase “as usedin this document shall mean” or similar language (e.g., “this termmeans,” “this term is defined as,” “for the purposes of this disclosurethis term shall mean,” etc.). References to specific examples, use of“i.e.,” use of the word “technology,” etc., are not meant to invokeexception (b) or otherwise restrict the scope of the recited claimterms. Other than situations where exception (b) applies, nothingcontained in this document should be considered a disclaimer ordisavowal of claim scope.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this technology belongs. It willbe further understood that terms, such as those defined in commonly useddictionaries, should be interpreted as having a meaning that isconsistent with their meaning in the context of the present applicationand relevant art and should not be interpreted in an idealized or overlyformal sense unless expressly so defined herein. While not explicitlydefined below, such terms should be interpreted according to theircommon meaning.

In addition, where features or aspects of the disclosure are describedin terms of Markush groups, those skilled in the art will recognize thatthe disclosure is also thereby described in terms of any individualmember or subgroup of members of the Markush group.

Unless the context indicates otherwise, it is specifically intended thatthe various features of the technology described herein may be used inany combination. Moreover, the disclosure also contemplates that incertain embodiments, any feature or combination of features set forthherein may be excluded or omitted. To illustrate, if the specificationstates that a complex comprises components A, B and C, it isspecifically intended that any of A, B or C, or a combination of any twoor more thereof, may be omitted and disclaimed singularly or in anycombination.

Unless explicitly indicated otherwise, all specified embodiments,features, and terms intend to include both the recited embodiment,feature, or term and biological equivalents thereof.

All patents, patent applications, provisional applications, andpublications referred to or cited herein are incorporated by referencein their entirety, including all figures and tables, to the extent theyare not inconsistent with the explicit teachings of this specification.

Other embodiments are set forth in the following claims.

1.-20. (canceled)
 21. A method for producing a composition with a gassyaroma, the method comprising: mixing a terpene compound with anorganosulfur compound to form a composition; wherein: the organosulfurcompound comprises prenyl mercaptan, 2-methylthiophene,3-methylthiophene, dimethyl disulfide, diprenyl disulfide,3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, or dimethyl sulfide; and the terpene compound comprisesmyrcene, β-caryophyllene, limonene, α-pinene, β-pinene, valencene,ocimene, terpinolene, humulene, linalool, bisabolol, nerol,phellandrene, terpineol, farnesene, fenchyl alcohol, geraniol, menthol,citronellol, citronellal, geranyl acetate, nerolidol, or citral.
 22. Themethod of claim 21, wherein the composition is an edible composition, anaerosol composition, a flavor composition, a fragrance composition, oran inhalable composition.
 23. The method of claim 21, wherein thecomposition comprises about 0.000001 wt % to about 0.3 wt % of theorganosulfur compound, based on the total weight of the composition. 24.The method of claim 21, wherein the organosulfur compound comprisesprenyl mercaptan, prenylthioacetate, or 2-methylthiophene.
 25. Themethod of claim 21, wherein the terpene compound is present in thecomposition from about 0.1 wt % to about 99 wt %, based on the totalweight of the composition.
 26. The method of claim 25, wherein theterpene compound is present in the composition from about 0.01 wt % toabout 50 wt %, based on the total weight of the composition.
 27. Themethod of claim 21, wherein the composition is an edible composition.28. The method of claim 27, wherein the edible composition is a food ora beverage.
 29. The method of claim 28, wherein the beverage is beer, analcohol containing beverage, or a non-alcohol containing beverageproduct.
 30. The method of claim 21, wherein the composition is aninhalation composition.
 31. The method of claim 21, wherein thecomposition is a flavor and/or fragrance composition.
 32. A method fordetecting one or more sulfur-containing compounds in a cannabis plant,the process comprising: analyzing the headspace gas from a cannabisplant sample using a one- or a two-dimensional gas chromatograph coupleda sulfur chemiluminescence detector (SCD); wherein the sulfur-containingcompound is selected from the group consisting of prenyl mercaptan,2-methylthiophene, 3-methylthiophene, dimethyl disulfide, diprenyldisulfide, 3-methyl-2-buten-1-yl thiolacetate,3-methyl-1-[(3-methyl-2-buten-1-yl)sulfanyl]-2-butene, prenylmethylthiol(1-(methylsulfanyl)-3-methyl-2-butene), prenyl thioacetate,thiogeraniol, dimethyl sulfide, and a combination of any two or morethereof.
 33. The method of claim 32, wherein the gas chromatograph is atwo-dimensional gas chromatograph.
 34. The method of claim 32, whereinthe gas chromatograph is further coupled with one or more of a massspectrometer (MS), flame ionization detector (FID), nitrogenchemiluminescence detector (NCD), a nitrogen phosphorus detector (NPD),an atomic emission detector (AED), a flame photometric detector (FPD),and an electron capture detector (ECD).
 35. The method of claim 34,wherein the mass spectrometer is a time-of-flight mass-spectrometer. 36.The method of claim 32, wherein the cannabis plant sample comprises adried flower, dried ground flower, a wet flower, or a flower extract.37. The method of claim 36, wherein the cannabis plant sample comprisesa dried ground flower.
 38. The method of claim 32, wherein thesulfur-containing compound comprises prenyl mercaptan, prenylthioacetate, prenylthioacetate, or 2-methylthiophene.
 39. The method ofclaim 38, wherein the sulfur-containing compound comprises prenylmercaptan or prenyl thioacetate.